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Christmas Crossdressing

15 Posts
9 Users
42 Reactions
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Posts: 793
Duchess
Topic starter
(@gracepal)
Noble Member     South Carolina, United States of America
Joined: 4 months ago

Here’s a question I have for this chilly December morning as I sip coffee…

Before I became a part of the “Wonderful World of CDH”, every holiday season I would google Christmas Crossdressers or something similar and get to see lots and lots of girls in their Christmas finery, decorating trees, posing in their holiday dresses and costumes. It really got me in the Christmas spirit although I wasn’t dressing myself at the time. I would always think: “I want to do that!” So this year I ordered my Mrs. Claus’s Helper outfit and my candy cane pantyhose and had a BLAST yesterday taking pictures of “Holiday Grace”. (Private photos gallery girls😉)

But that got me to thinking…do the ladies here on CDH have any annual holiday traditions involving their crossdressing that they partake of ? Or maybe a good holiday crossdressing experience or story to share? I’m always on the hunt for new ideas within reason…(or maybe outside of reason🤣)

I realize Halloween is a biggie, but it seems to me that I find way more Christmas Crossdressing photos of girls online than i do of Halloween ones.

So ladies - any Holiday escapades you’d like to share with us for this Yuletide season?

GP

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14 Replies
2 Replies
Lady
(@kimdl94)
Joined: 8 months ago

Reputable Member     Longview, Texas, United States of America
Posts: 167

@gracepal I don’t do much for Halloween, since I don’t go to bars and that sort of thing.   My personal holiday outing is an evening at a favorite restaurant.  Every year I buy myself a seasonally appropriate outfit, a bit dressier than my everyday casual style, enjoy a couple of drinks and a good meal.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3847

Posted by: @gracepal

Here’s a question I have for this chilly December morning as I sip coffee…

Or maybe a good holiday crossdressing experience or story to share?

So ladies - any Holiday escapades you’d like to share with us for this Yuletide season?

Lately, I bought some very deep colours of nail polish in red and green. Appropriate for Christmas. I started off with the red. Nobody said a word. So I switched to the very dark green (my wife thought that it was black) and it took a while, but I finally got a rise out of someone in a store.

Today, I had a dental checkup. The dental hygienist knows me well and is talkative. Yes, we talked about my nails. When I went to check out, I finally got a response from one of the office managers who looked after me. The two who did not respond were the two who replaced a tiny filling. Two out of four ain't bad.

I have repaired and relayered the polish so much that I will have to start from scratch again.

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Posts: 3847
Lady
(@harriette)
Illustrious Member     Toronto, Ontario, Canada
Joined: 2 years ago

For my first time, I have been wearing the two main Christmas coloured nail polishes - a bright, deep red and a very evergreen green - continuously in public. Not mixed at the same time yet, but I am still learning.

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Posts: 59
Duchess Annual
(@rayna)
Estimable Member     Leominster, Massachusetts, United States of America
Joined: 4 months ago

I haven't dressed up over the holiday season but I've always wanted to. I remember looking at all the Christmas catalogs with all the beautiful dresses and outfits and wanting so badly to be able to get dressed up like that. Now my schedule is more free, and I'm looking for things to do and events I could go to while I'm dressed. They'll have to be CD friendly, of course, given my overall looks and proportions. 

 I do have a new dress on order, it's more New Years-y than Christmas-y, though. So I'm leaning a bit more toward going out for New Year's Eve than for Christmas Eve. I also have a green lace dress that I've had for many years that would work for Christmas. I recently put it on and took a photo of myself and posted it on my profile. It's a nice vintage look but I think I'd like something a little more modern. 

 It's such a busy time of year, though, and it might not be easy to work dressing up into my regular schedule. We'll see. But it can't hurt to be prepared, right? 

Rayna

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Posts: 45
Lady
(@kat9476)
Trusted Member     Seattle, Washington, United States of America
Joined: 3 years ago

My wife and I both WFH for last several years , so we started a tradition of having a “home office” party together the week before Christmas, we dress in holiday style outfits, make a Charcuterie board and share a bottle of wine or mimosas and crank up some Christmas tunes and exchange a very small early gift with each other while the house is “quiet”.

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Posts: 2022
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

Grace -

My wife and I bought some holiday dresses for each other and are going to spend Christmas Day at home having a girly Christmas  We're both looking forward to it. Sorry I don't do pictures so can't share here - part of our agreement.

Hope you have a wonderful holiday season.

XOXO
Suzanne

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3 Replies
Duchess
(@gracepal)
Joined: 4 months ago

Noble Member     South Carolina, United States of America
Posts: 793

@cdsue Suzanne, I like it! I’m guessing we’ll do a “Girls Holiday Night” this year. I even tolerate Hallmark Christmas movies much better when I’m in Grace mode. My wife has gotten me a couple of dressier dresses in recent days. Once in awhile she’ll try one on and I think she looks fantastic in them. But she’ll say, “no, that’s for Grace”. It’s been alluded to on CDH that we dress the way we like our women to look and it’s certainly my case. Everytime she models a “Grace dress” it’s a winner for me. Women just don’t wear that stuff in their everyday lives anymore though. Long live crossdressing🥰

As for no pics, I get it. You’ll never be outed if there aren’t any. And any is too many. You have to put family first over anything else. When I resumed Grace my wife inquired about there being any old pictures of her out there in the ether. That was an easy answer of no. My policy back then was no pics of me, ever. (Of course, now I wish I had some. I had a “Farah” style of wig back in my youth! My recollection is I was quite the hottie….RIGHT.)🤣

GP

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Hostess
(@cdsue)
Joined: 5 years ago

Famed Member     Delaware, United States of America
Posts: 2022

@gracepal thanks - I like Hallmark movies but as you say better when I'm in Suzanne mode.

That's wonderful that your wife got Grace some new dressier dresses and better yet that she has tried them on. I agree that we dress the way we would like our women to dress. My wife calls me her fashionista when we go shopping as she feels I have better taste in women's clothes - wonder why? Yes - long live crossdressing.

Thank you for understanding about pictures. It is a shame you don't have any from your Farah Fawcett days I'm sure you were hot then as you are now.

XOXO
Suzanne

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Duchess
(@gracepal)
Joined: 4 months ago

Noble Member     South Carolina, United States of America
Posts: 793

@cdsue Hot now? That’s funny, but thanks Suzanne. Yeah, the ol Farah Fawcett days were quite memorable for me. I certainly had a lot of drinks bought for me so that was a good indicator I figure…never drank them though as usually back then, they were from men. The girls I hung with - we bought our own🥰 Fun memories though for sure.

GP

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Posts: 128
(@katiep)
Reputable Member     Nottinghamshire, United Kingdom
Joined: 2 months ago

My wife has invited Katie for Christmas lunch for the first time which pleased me as you can imagine. So should it be a formal dress or relaxed comfortable skirt and blouse, I need to start ordering. I do have a new wig and false nails, they need painting, so much to think about. Also my wife suggested I think about what I shall be wearing for New Year’s Eve. We are lucky there is only the two of us. Katie.

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2 Replies
Duchess
(@gracepal)
Joined: 4 months ago

Noble Member     South Carolina, United States of America
Posts: 793

@katiep Christmas lunch Katie, very nice! I’d wear a dress but probably not too formal as comfort is important when you’re chowing down.🥰

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(@katiep)
Joined: 2 months ago

Reputable Member     Nottinghamshire, United Kingdom
Posts: 128

@gracepal I was shocked myself, I guess I am very very lucky.

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Posts: 1658
Baroness
(@annaredhead)
Famed Member     Cornwall, United Kingdom
Joined: 10 months ago

Tradition - no, but I have ordered several pairs of festive tights

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Posts: 345
Duchess
(@philma)
Honorable Member     Kansas City, Missouri, United States of America
Joined: 5 years ago

My wife and I used to do Santa Con in KC and I dressed ip in a Mrs. Claus dress, shiny nude tights, t-strap heels, nails & eyelashes & makeup.  I also wore a full beard I painted white.  My wife wore a Santa outfit (without stuffing) and one of those hats with the attached fuzzy beard.  We made name tags that said Mr. & Mrs. Cross Kringle (I wore Mrs).  We were a hit!  TONS of people taking pictures with me.  LOTS of compliments on my legs (I do have great legs in hose… I’m a runner & cyclist).  One lady asked me “So, are you a dude?”  That got me thinking I might be able to pass and ultimately led to my first public outing as Philma with my wife!  

I’ve since moved from KC and the change in jobs has limited my time and is public enough that much I cannot safely get out undetected.  It us NOT safe here to get clocked.  I was hoping to go to a Christmas house in party in Dallas I was told about on Meetup, but I can’t afford the hotel room.  Sorry to dump here.  It’s been a tough fall season.  I’m dying to get out!! 

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